diff --git a/tests/data_files/Makefile b/tests/data_files/Makefile
index 669b406..0429bdd 100644
--- a/tests/data_files/Makefile
+++ b/tests/data_files/Makefile
@@ -202,6 +202,10 @@
 	$(FAKETIME) '2015-09-01 14:08:43' $(OPENSSL) req -x509 -new -subj "/C=UK/O=mbed TLS/CN=mbed TLS Test intermediate CA 3" -set_serial 77 -config $(test_ca_config_file) -extensions noext_ca -days 3650 -sha256 -key $< -out $@
 all_final += server5-ss-forgeca.crt
 
+server5-tricky-ip-san.crt: server5.key
+	$(OPENSSL) req -x509 -new -subj "/C=UK/O=Mbed TLS/CN=Mbed TLS Tricky IP SAN" -set_serial 77 -config $(test_ca_config_file) -extensions tricky_ip_san -days 3650 -sha256 -key server5.key -out $@
+all_final += server5-tricky-ip-san.crt
+
 server10-badsign.crt: server10.crt
 	{ head -n-2 $<; tail -n-2 $< | sed -e '1s/0\(=*\)$$/_\1/' -e '1s/[^_=]\(=*\)$$/0\1/' -e '1s/_/1/'; } > $@
 all_final += server10-badsign.crt